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I installed the desktop manager and Playbook looked like a USB drive on my windows 7 PC.
then drag n drop your videos in the the playbook\video folder
these should help with video transfer
Media types that are supported on the BlackBerry PlayBook
How to synchronize media from a computer to a BlackBerry PlayBook
How to transfer files to and from the BlackBerry PlayBook
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I download youtube videos directly to my playbook by using filsh.net